CN101784703B - Thermoset resin fibres - Google Patents
Thermoset resin fibres Download PDFInfo
- Publication number
- CN101784703B CN101784703B CN200880104340.1A CN200880104340A CN101784703B CN 101784703 B CN101784703 B CN 101784703B CN 200880104340 A CN200880104340 A CN 200880104340A CN 101784703 B CN101784703 B CN 101784703B
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- CN
- China
- Prior art keywords
- composite
- fibre
- thermoset resin
- composition
- resin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000004634 thermosetting polymer Substances 0.000 title claims abstract description 124
- 239000000835 fiber Substances 0.000 claims abstract description 369
- 239000002131 composite material Substances 0.000 claims abstract description 152
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 93
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 35
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 24
- 238000004519 manufacturing process Methods 0.000 claims abstract description 19
- 239000000203 mixture Substances 0.000 claims description 196
- 239000003795 chemical substances by application Substances 0.000 claims description 78
- 238000007711 solidification Methods 0.000 claims description 7
- 230000008023 solidification Effects 0.000 claims description 7
- 239000004695 Polyether sulfone Substances 0.000 claims description 6
- 229920006393 polyether sulfone Polymers 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 230000008014 freezing Effects 0.000 claims description 4
- 238000007710 freezing Methods 0.000 claims description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 4
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
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- 229920002873 Polyethylenimine Polymers 0.000 description 2
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- DDTKYVBFPULMGN-UHFFFAOYSA-N 2-methyl-6-propan-2-ylaniline Chemical compound CC(C)C1=CC=CC(C)=C1N DDTKYVBFPULMGN-UHFFFAOYSA-N 0.000 description 1
- UIDDPPKZYZTEGS-UHFFFAOYSA-N 3-(2-ethyl-4-methylimidazol-1-yl)propanenitrile Chemical compound CCC1=NC(C)=CN1CCC#N UIDDPPKZYZTEGS-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
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- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
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- B29C70/465—Shaping or impregnating by compression not applied for producing articles of definite length, i.e. discrete articles using matched moulds, e.g. for deforming sheet moulding compounds [SMC] or prepregs and impregnating by melting a solid material, e.g. sheets, powders of fibres
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B29C70/04—Shaping composites, i.e. plastics material comprising reinforcements, fillers or preformed parts, e.g. inserts comprising reinforcements only, e.g. self-reinforcing plastics
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- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/60—Nonwoven fabric [i.e., nonwoven strand or fiber material]
- Y10T442/659—Including an additional nonwoven fabric
- Y10T442/668—Separate nonwoven fabric layers comprise chemically different strand or fiber material
- Y10T442/669—At least one layer of inorganic strand or fiber material and at least one layer of synthetic polymeric strand or fiber material
Abstract
The present invention relates to thermoset resin fibre components (10, 30, 40, 44, 50, 210, 310, 410), composite materials (12, 26, 28, 29, 34, 36, 43, 48, 54, 58, 62) comprising thermoset resin fibre components, composite articles manufactured using such composite materials and methodologies for manufacturing same. The thermoset resin fibre components may comprise a single fibre of thermoset resin or a plurality of fibres commingled together. The properties and characteristics of the thermoset resin used are chosen according to the materials to be produced therefrom. The thermoset fibre components may be woven into reinforcement fibres (14, 31, 38, 114, 214, 314, 60, 414) to form prepregs. Thermoplastic fibres (32, 46, 52) may be commingled and co-woven with the thermoset fibre components.
Description
Technical field
The present invention relates to thermoset resin fibres, especially but not only relate to the thermoset resin fibres for the manufacture of fibre reinforced composites and composite product.
Background technology
Fibre reinforced composites generally include the fortifying fibre in curable resin matrix.Fortifying fibre is insoluble in resinous substrates, is generally used for making resinous substrates hardening strengthening, thereby it is strengthened, especially once be cured.This type of suitable fortifying fibre comprises carbon, glass, aramid fiber, pottery and other fibers known in those skilled in the art.
The comprehensive physical chemical characteristic of composite mesostroma resin and fortifying fibre is generally: in the time that this combination is cured, the composite product obtaining has sizable intensity, and relatively light weight characteristic, make specific examples of such components can in much industry, obtain many application, comprise Aero-Space, automobile, boats and ships and civil engineering industry.Carefully select resin and fiber to produce composite and the composite product with desirable characteristics, this is known to those skilled in the art.
The method of the goods that have many known formation fibre reinforced composites and made by fibre reinforced composites.Have many relate to be placed on utensil or mould with before solidifying to form composite product by the method for matrix resin and fortifying fibre combination.Select in advance the combination that is usually expressed as plate shape or the fortifying fibre with shape and matrix resin as prepreg.The merits and demerits of known prepreg structure is known for those skilled in the art.
The additive method of manufacturing fibre reinforced composites comprises inserts dry fortifying fibre in utensil or mould, then uses such as the technology of resin transfer molding and liquid resin form resin perfusion is become to fiber.The merits and demerits of this resinoid form technology is also known in those skilled in the art.
Conventionally, matrix resin comprises thermosetting resin, such as epoxy resin, cyanate, BMI or its combination.In the time manufacturing prepreg, thermosetting resin is fed on fortifying fibre layer fully to flood or partly to flood this layer according to known technology conventionally.Thereby matrix resin can liquid form be directed into and forms resin bed on fortifying fibre layer partly to flood or impregnation of fibers layer fully on fiber, or can be used as and be placed in fibrolaminar lip-deep preformed layer and import.In this prepreg, matrix resin generally includes thermosetting resin and promotes thermosetting resin cured curing agent.Therefore, the pot-life of this type of prepreg is limited, often need to the pot-life be extended to realistic scale by freezing or stored under refrigeration.
In resin form technology, matrix resin imports with the fibrage of impregnation drying fully during curing with liquid form conventionally.Thermosetting resin is also imported into conventionally together with curing agent, often in conjunction with the condition with high temperature and/or high pressure, makes thermosetting resin cured in fortifying fibre structure, forms thus composite material compositions or the goods with fiber reinforced resin based matter.
Adopt the technology of these known generation fibrous composite goods, its target is the formation that prevents or reduce as far as possible the interior unwanted air pocket of curing fibre reinforced composites goods or hole, because these can cause defect in finished product.When uncured prepreg is placed in mould or utensil when forming goods, can need the prepreg of some to be stacked on the top of other prepregs.Air often remains between each layer, and has multiple technologies during curing process, to remove these air pockets for assisting.But these technology relate to complicated and expensive technique and device, such as producing necessary condition with the autoclave from driving away between resin bed by air.
Other forms of composite does not contain fortifying fibre.For example, resin adhesive often comprises the combination of liquid thermosetting resin and other components such as curing agent, catalyst, curing agent etc.For fear of the premature cure of this type of material, adding before adhesive, thermosetting resin and curing agent are often separated.But, like this can be inconvenient, this be for will may be favourable with scheduled volume provides together accurately thermosetting resin and curing agent, but conventionally can make the pot-life relatively short.
Summary of the invention
According to the present invention, provide a kind of curable thermoset resin fibre components for the manufacture of composite.
Thermoset resin fibre components can comprise many thermoset resin fibres.Fiber in thermoset resin fibre components can be continuous and/or discontinuous, unidirectional, twisting and/or tangle.
Thermoset resin fibre components preferably includes one or more in epoxy resin, cyanate ester resin, BMI (BMI), Polybenzoxazine, polyimides, phenolic resins, polyester.Fiber in fibre composition can comprise that the admixture of some thermosetting resins and/or composition can comprise the many different fibers that comprise different thermosetting resins and/or its admixture.
Thermoset resin fibre components can comprise additive, all if one or more thermoplastics that thermosetting fibre composition is especially toughened in the time solidifying.This additive may be dissolved in thermoset resin fibre components.Preferably, thermoset resin fibre components comprises a small amount of curing agent or does not comprise curing agent.This will give thermoset resin fibre components with the relatively long pot-life.Alternatively, thermosetting fibre composition can comprise curing agent, but curing agent is preferably limited to promote solidifying under condition of storage, and for example, curing agent can be suppressed under relative low temperature, and thus as point be kept at refrigeration or freezing conditions curing agent of lower time suppressed.
Preferably, thermoset resin fibres is normally inviscid, and is easy to manual disposal.Preferably, the viscosity of thermosetting resin at 23 ℃ of temperature is greater than 5 × 10
4pas, is more preferably greater than 2 × 10
5pas.Preferably, during curing viscosity drops to 2 × 10
3below Pas.
Preferably, fibre composition has the diameter of 3～50 microns, and most preferably has the diameter of 5～10 microns.
Preferably, when by stored frozen, composition has more than 12 months pot-lives, and if preferably have the pot-life of 3-12 month in the lower preservation of room temperature (18 ℃-23 ℃).
Preferably, curable thermosetting fibre composition comprises N, N, N, N-four glycidyl group-4 ' 4-diaminodiphenyl-methane and polyether sulfone.Preferably, polyether sulfone is dissolved in N, N, and N, in N-four glycidyl group-4 ' 4-diaminodiphenyl-methane.
Preferably, thermoset resin fibre components comprises the resin system according to a further aspect in the invention of part, and this system further comprises the curing agent that can promote that thermoset resin fibre components is curing.
Curing agent can be in the time occurring to solidify or before be fed to soon in thermoset resin fibre components, likely use the technology that is similar to resin perfusion.Composite is stable in this way, because can not solidify significantly in the time lacking requisite curing agent, has thus the relatively long pot-life.
Alternatively or additionally, curing agent can combine with thermoset resin fibre components, but take not promote thermosetting resin cured form.For example; curing agent can be solid, such as particle or fibers form, or other high viscosity forms; to reduce and the contacting and interaction of thermoset resin fibres, the solidification between them in suitable condition of storage such as refrigeration and freezing time relatively slowly or is substantially avoided.
Curing agent can comprise one or more catalyst, curing agent.The example of suitable curing agent comprises dicyan imines, 4,4 '-diamino diphenyl sulfone, 3,3 '-diamino diphenyl sulfone, 4,4 '-di-2-ethylhexylphosphine oxide (2,6 '-diethylaniline), 4,4 ' di-2-ethylhexylphosphine oxide (2-isopropyl-6-methylaniline), 3,5 '-diethyl Toluene-2,4-diisocyanate, 4/2,6-diamines, N, N '-(methyl isophthalic acid, 3-benzene) two [N, N '-dimethyl ureas], 1-(2-cyanoethyl)-2-ethyl-4-methylimidazole.
According to another aspect of the present invention, provide a kind of composite, it comprises curable thermoset resin fibre components and fortifying fibre composition.
Thermoset resin fibre components can comprise many thermoset resin fibres, and can be as described in any one paragraph in 13 paragraphs above.Preferably the external diameter of each fibre composition is substantially the same, is preferably 5-7 micron for carbon-reinforced fiber composition, is 15-20 micron for fiberglass reinforcement composition.
Fortifying fibre composition can comprise one or more in carbon, glass, aramid fiber, pottery.Thermoset resin fibre components is 50 with the ratio that strengthens resin fibre composition: 50-10: 90v/v.
Thermoset resin fibre components can comprise part resin system, and system according to the invention comprises composite and the curing agent described in 3 paragraphs above.Preferably, thermoset resin fibre components is arranged on the position not contacting with curing agent until need cure curable thermoset resin fibres.Curing agent is preferably liquid under processing temperature.
Alternatively or additionally, curing agent can be solid, such as fiber or particle, in the case, can between some or all of thermoset resin fibres and curing agent, come in contact, but their physical property and/or condition of storage to make the solidification between them relatively slowly or substantially be avoided.
Resin system can further comprise other additives, such as thermoplastic.
Some or all fortifying fibres in fiber or fortifying fibre composition can be by braiding, sew up, continuously or discontinuously, uniaxially or random orientation ground is short cuts, twists, tangles or in fact take any suitable structure for the production of composite product.
Thermoset resin fibre components and fortifying fibre composition can be by mixing such as braiding, stitching, twisting and/or entanglement.One or more thermoset resin fibres can around and twist together along the length of one or more fortifying fibre, and/or vice versa.Alternatively or additionally, the structure that thermoset resin fibre components and fortifying fibre composition can be substantially in parallel extends mutually abreast.
Alternatively or additionally, composite can be included in the thermoset resin fibres layer and the fortifying fibre layer that on a surface at least separately, contact.Each fibrage can be by braiding, sew up, continuously or discontinuously, uniaxially or configuration randomly, and can take the form of plate, fabric or felt.
Thermosetting resin composition can be by braiding, sew up, or penetrate in addition in fortifying fibre composition, thereby be substantially evenly distributed in wherein, and may run through this enhancing ingredients, or in the one or more predetermined of this fortifying fibre composition and the location selected.
Alternatively or additionally, fortifying fibre composition can or penetrate in thermoset resin fibre components in addition by braiding, stitching, thereby be substantially distributed in equably and preferably run through this thermoset resin fibre components, or being distributed in the region of the one or more predetermined and selection in this thermoset resin fibre components.
According to another aspect of the present invention, provide a kind of composite, it comprises curable thermoset resin fibre components and other non-fortifying fibre composition.
Thermoset resin fibre components is preferably described above.
Non-fortifying fibre composition can comprise thermoplastic fibre composition, then this composition can comprise many thermoplastic fibres.
Thermoplastic fibre composition can comprise one or more thermoplastic polymers such as polyethylene, polypropylene, polyamide, polyether-ether-ketone, polyethylene terephthalate, polyether sulfone, PEI, polyarylsulfone (PAS), polyphenylene sulfide, polyimides, polysiloxanes and all kinds of rubber.Thermoplastic fibre or at least some thermoplastic fibres can be hemicrystalline.
Preferably, the effect of thermoplastic fibre composition is that composite is especially toughened when curing.
Preferably, the ratio of thermoset resin fibres and non-fortifying fibre composition is 90/10-70/30, and 80/20v/v most preferably.
Alternatively or additionally, non-fortifying fibre composition can comprise curing agent, one or more of all curing agent as described herein.
Thereby thermoset resin fibre components and non-fortifying fibre composition can mix the composite forming described in arbitrary paragraph above.
Preferably, composite comprises the part resin system that can further comprise curing agent, or further comprises the curing agent that can promote that thermosetting resin composition is curing.This curing agent can be curing agent as above.
Therefore, the present invention further provides resin system as in the previous paragraph.
According to another aspect of the present invention, provide a kind of composite, it comprises thermoset resin fibre components, non-fortifying fibre composition and fortifying fibre composition in addition.
Preferably, thermoset resin fibre components is composition as above.
Preferably, non-fortifying fibre composition is composition as above.
Preferably, fortifying fibre composition is composition as above.
Preferably, fibre composition by such as braiding, twisting, stitching, entanglement, threading or arbitrarily other suitable modes mix, and can form together plate, band or other prefabricated blank.Various fibre compositions in material can be evenly distributed in composite substantially, and run through as required this composite.Alternatively or additionally, can select and pre-determine the position of each fibre composition and consumption so that the material with desirable characteristics and the cured article be made up of them to be provided, desirable characteristics is such as the region with relatively high resin toughness, has the region of relatively high and/or low Vf.
Two kinds in three types fiber can mix in some way, and for example together, then the fiber of these two kinds of fibers and the third type in an identical manner or the optional different modes such as braiding, threading, stitching and mixing in twisting.
Composite can be included in setting up period and need to soak fully all resins of fortifying fibre composition.But, in some embodiments, thermosetting resin, comprise non-fiber thermosetting resin, can be included in or be added in composite and/or resin can further during curing be directed on material, such as by resin perfusion technique, or another composition that can be used as material provides, such as the resin as resin bed or the spacer region place discrete magnitude on material surface.
Non-fortifying fibre composition can become to separate by strengthening resin fibre with thermoset resin fibre components, prevents from thus coming in contact between non-fortifying fibre composition and thermoset resin fibre components.In the time that non-enhancing ingredients comprises curing agent, can be useful especially like this.
According to another aspect of the present invention, provide a kind of method of manufacturing composite product, the method comprises makes curable thermoset resin fibre components stand condition of cure completely or partially to solidify this composition.
According to another aspect of the present invention, provide a kind of method of manufacturing composite product, comprised and make composite as described above stand condition of cure.
Thermoset resin fibre components or composite can with curing agent start when curing process or before mix soon, in the case, curing agent is fed in resin fibre composition preferably as liquid, and is preferably directly directed into and on it, has placed mould or the utensil for molded and shaped and curing fibre composition or composite.Fibre composition or composite can be taked the form of prefabricated blank.
Alternatively, or additionally, curing agent can be used as solid, such as particle or fiber, is directed in resin fibre composition or composite.
Alternatively, or additionally, curing agent can be included in composite, and promotes its solidification by applying condition of cure.
According to a further aspect in the invention, providing a kind of uses curable thermoset resin fibre components and makes this composition stand to make the curing condition of this thermoset resin fibres and the composite product manufactured.
According to a further aspect in the invention, provide a kind of by the composite product that composite as above is stood the condition of this composite material solidification is manufactured.
These conditions can comprise curing agent is directed in thermoset resin fibre components and/or composite, and can comprise and use curing agent infused composite.
Accompanying drawing explanation
Now will be only by means of embodiment, with reference to accompanying drawing, embodiments of the present invention are described, wherein:
Fig. 1 a is the schematic diagram according to thermoset resin fibre components of the present invention;
Fig. 1 b is the cross sectional representation of the thermoset resin fibre components of Fig. 1 a;
Fig. 1 c is the schematic diagram that is applicable to the device of producing thermoset resin fibres of the present invention;
Fig. 2 is according to the longitudinal cross-section schematic diagram of the composite that comprises thermoset resin fibre components and fortifying fibre composition of the present invention;
Fig. 3 is according to the longitudinal cross-section schematic diagram of the composite that comprises thermoset resin fibre components and fortifying fibre composition of optional embodiment of the present invention;
Fig. 4 a is according to the longitudinal cross-section schematic diagram of composite of comprising of another embodiment of the present invention curable thermoset resin fibre components and fortifying fibre composition;
Fig. 4 b is the longitudinal cross-section schematic diagram according to another composite of the present invention;
Fig. 4 c is the lateral cross schematic diagram of an embodiment of the composite of Fig. 4 b;
Fig. 4 d is the lateral cross schematic diagram of another embodiment of the composite of Fig. 4 b;
Fig. 5 a is the schematic diagram that comprises the composite of curable thermoset resin fibre components and other fibre composition;
Fig. 5 b is the schematic diagram that comprises another composite of thermoset resin fibre components and other fibre composition;
Fig. 6 is according to another embodiment of the composite that comprises curable thermoset resin fibre components and thermoplastic fibre composition of the present invention;
Fig. 7 is according to the schematic diagram of the composite that comprises thermoset resin fibre components, thermoplastic fibre composition and fortifying fibre composition of an embodiment of the invention;
Fig. 8 is according to the longitudinal cross-section schematic diagram of the composite that comprises thermoset resin fibre components, thermoplastic fibre composition and fortifying fibre composition of another embodiment of the present invention;
Fig. 9 is according to the cross sectional representation of the composite that comprises thermoset resin fibre components, thermoplastic fibre composition and fortifying fibre composition of another embodiment of the present invention;
Figure 10 is the longitudinal cross-section schematic diagram according to the composite of another embodiment of the present invention;
Figure 11 is the longitudinal cross-section schematic diagram according to the composite of another embodiment of the present invention;
Figure 12 is the longitudinal cross-section schematic diagram according to the composite of another embodiment of the present invention;
Figure 13 is the explanation schematic diagram of manufacturing the method for composite of the present invention;
Figure 14 manufactures according to the explanation schematic diagram of the optional method of composite of the present invention;
Figure 15 be arranged in for curing die device according to the schematic diagram of multilayer materials of the present invention or prefabricated blank, and;
Figure 16 is that the present invention is for the intrafascicular schematic diagram of piddler.
The specific embodiment
The present invention relates to thermoset resin fibre components, comprise the composite of thermoset resin fibres and composite product and the manufacture method thereof that uses this composite to manufacture.
Fig. 1 is the schematic diagram for the manufacture of a part for the curable thermosetting fibre resinous principle 10 of composite.
Fig. 1 b illustrates the cross section of upper this fibre composition of direction Ib.Fiber can be by for example twisting together, or mix to form filamental thread or yarn by other suitable methods arbitrarily.With the characteristic of thermosetting resin and feature select according to the material that will produce it.Fiber in thermosetting fibre composition or one or more fiber can be the admixtures of thermosetting resin.Alternatively, or additionally, different fibers in thermoset resin fibre components can comprise different resins, for example make, composition can comprise two kinds of dissimilar fibers, every kind of fiber is made up of the admixture of a kind of resin or resin, thereby has the combination that is different from other resin that forms admixture.Therefore, for example, the fiber of a type can comprise epoxy resin, and another kind can comprise cyanate ester resin.In another kind of alternative, what thermosetting fibre composition can comprise two or more types forms different fibers separately, because they comprise the admixture of same resin separately, but resin in admixture exists with different amounts.For example, the fiber of a type can comprise the admixture of epoxy resin, and the another kind of fiber in composition can comprise the different admixtures of identical epoxy resin.The character of any additive in composition can be identical or changes according to fiber dissimilar in composition.
The present invention makes those skilled in the art can prepare resin combination and they is added in thermoset resin fibre components to generate the goods that have the curable composites of required physicochemical characteristics and be made up of it with the form of fiber.
Suitable thermosetting resin comprises epoxy resin, cyanate ester resin, BMI (BMI), Polybenzoxazine, polyimides, phenolic resins, polyester and other resins well known by persons skilled in the art.
In some embodiments, thermoset resin fibre components 10 does not comprise curing agent.This guarantees that fibre composition 10 is stable, thereby gives fiber 10 with relatively long storage life or pot-life.
But embodiment is below also included within scope of the present invention: some curing agent can be included in fibre composition 10, do not promote thermosetting resin cured form but preferably take to stand specific condition with startup or before accelerating to solidify.
Fig. 1 c has shown that generation is according to the straightforward procedure of thermoset resin fibre components 10 of the present invention.Head or spinning head that liquid thermosetting resin (fusing) consists of the opening H in the base portion B by storage tank T are discharged.Can exert pressure to order about resin and pass through head.In the time that resin fibre F sprays from the base portion of storage tank, they are cooled gradually, thereby it was solidified before being collected into winding wheel T.
If storage tank T is static, thermoset resin fibres F will comprise single thermoset resin fibres or sub-thread thermosetting resin, and every or per share corresponding to thermoset resin fibre components 10 of the present invention.
If storage tank T is around vertical axis revolving,, in the time that fiber F sprays from head, they are twisted together mutually.Then this twisted yarn or thermoset resin fibre components 10 are collected in the winding wheel of processing for forward.
The device of Fig. 1 c has only shown from wherein having sprayed 4 strands or 4 thermoset resin fibres F.But the number that should be understood that opening H can be single opening to several thousand openings.
In the time that storage tank T adds the thermosetting resin formula of single type, this manufacture method can produce the thermosetting fibre composition of single formula.
But storage tank T can be subdivided into multiple discrete chambers, each chamber can add different resin formulas.Make it possible to like this produce comprise have different resins composition and/or formula plurality of fibers according to thermoset resin fibre components 10 of the present invention.
Use N, N, N, N-four glycidyl group-4 ' 4-diaminodiphenyl-methane is manufactured suitable curable thermoset resin fibre components with being dissolved in polyether sulfone wherein.
The common touch of thermoset resin fibre components is got on inviscid, is therefore easy to manual disposal.Thermosetting resin composition 10 conventionally has at approximately 23 ℃ of temperature and is greater than 5 × 10
4pas, is more preferably greater than 2 × 10
5the viscosity of Pas.As discussed above, during curing, viscosity drops to 2 × 10
3pas is following with facilitating impregnation.
Thermoset resin fibre components has 3～50 microns conventionally, most preferably the diameter of 5～10 microns.The size of fiber can design according to the fibre number in diameter and the composition 10 of the each fiber producing.
According to the thermosetting resin of this formula, when by stored frozen, there is more than 12 months pot-lives, and if there is the pot-life of 3-12 month in the lower preservation of room temperature (18 ℃-23 ℃).
Fig. 2 is the cross sectional representation that comprises the curable composites that is knitted into the as above curable thermoset resin fibre components 10 in fortifying fibre composition 14.In institute's drawings attached, thermosetting resin composition shows with the diameter amplifying.Clear in order to illustrate like this.Conventionally preferably, the diameter of thermosetting resin composition is identical or approaching with other fibre compositions in composite, thereby is convenient to fiber packing.
Fortifying fibre composition 14 can be by the material of any known type, such as carbon, glass, aramid fiber, pottery or well known to a person skilled in the art that other materials makes.
Fortifying fibre composition 14 can be braiding, that sew up, continuous, discontinuous, unidirectional, short felt that cut, unordered or well known to a person skilled in the art any other structures of this type of material.The fortifying fibre composition of Fig. 2 is the form of layer.
This type of composite 12 has many advantages.
First, thermoset resin fibre components 10 is stable, and because existence or the inhibition curing agent of restriction curing agent are avoided premature cure, this gives composite with good storage characteristics and relative long pot-life conventionally.
This equally distributed ability of fibre composition 10 makes resin be added in fibrage 14 with relatively little consumption, during curing still can realize dipping and " soaking " fully simultaneously, can produce thus the ratio of solidifying front fortifying fibre and thermosetting resin up to 90: 10 (90%vf), after solidifying, Vf drops to the composite of 55-65%Vf.
The fibers form of composition 10 also provides excellent discharge characteristic, because during curing fiber 10 hinders the movement of air and the eliminating of air thus indistinctively.
Another advantage is that common inviscid thermosetting fibre 10 can provide the material 12 with good operability.
According to conventional prepreg and prefabricated blank moulding process, composite 12 can be considered the form of prepreg or prefabricated blank, and can be cut into shape with moulding for being placed on mould or utensil.
Conventionally for the composite 12 that uses Fig. 2 produces curing composite product, according to the technical cure material 12 of common general knowledge.In composition itself, curing agent is not enough or there is no curing agent in the situation that, solidification process need to be directed into curing agent in thermoset resin fibre components 10.Curing agent generally comprises curing agent and catalyst, and is generally the liquid under processing temperature with very low viscous high flow.This makes promptly impregnation of fibers layer 14 of curing agent, and material 12 " is soaked ".As will be explained, the air in fibrage 14 is purged during the dipping of curing agent, and is during curing also purged.
Figure 15 is the schematic diagram that can be used to manufacture from composite according to the present invention the simple mould device 15 of composite product.Device 15 comprises mould or the utensil 16 with utensil surface 18, has placed the lamination 17 that comprises 3-layer composite material 12a, 12b, 12c on this surface.The upper and lower 12a, 12c comprise the composite 12 shown in Fig. 2, and middle level 12b shows about the composite described in Fig. 4 a.But character, number and the direction of the stacking composite being appreciated that can change, and can also conventionally be selected according to known technology according to the desirable characteristics of moulded products by those skilled in the art.In fact, lamination can comprise by any other these type of suitable materials of resin, dry fiber, veil, adhesive, the type heart, composite foam and conventional employing in the curing composite product of manufacture and the layer that structure forms.
This device comprises simple vacuum packet configuration, and it comprises the impermeable polymer bag 20 that is encapsulated in a usual manner lamination 17 exterior circumferential by sealing of hole 22.
Once required composite laminate 17 forms and is conventionally encapsulated under film 20, imports curing agent.Can use the technology that is similar to resin perfusion technique (such as resin transfer molding, liquid resin form and other technologies known in those skilled in the art) to complete this step.
As mentioned above, curing agent is imported into as the low-down liquid of viscosity, and promptly lamination 17 is soaked.Curing agent is conventionally heated to reduce viscosity before being directed into composite.Then the lamination 17 soaking is placed under suitable condition of cure, and this condition can relate to high temperature and/or vacuum condition.In Figure 15, show outlet 24, air is drawn out of to promote the removal of air by this outlet 20 and prevents that hole from forming from film.
Find to use the voidage of the composite product that composite of the present invention forms very little or there is no a space.The fibre property of thermosetting fibre composition is conducive to exhaust.Air in structure can be drawn out of through fiber before fiber is melted.In the time that temperature increases, thereby resinous principle fusing is soaked fortifying fibre.Up hill and dale and the equably ability in whole stratiform or other forms of fiber reinforcement material by thermosetting fibre component distributing, contribute to guarantee that total is curing equably, this can prevent the premature cure in the special area of composite conventionally, and avoid thus the air trapping that can occur in known configurations, in the situation of air trapping, resin is not evenly distributed in whole fiber-reinforced layer.
Fig. 3 is according to the cross sectional representation of the composite 26 of another embodiment of the present invention.In this embodiment, thermosetting fibre composition 10a, b and fortifying fibre composition 14 mix in two ways.As in the embodiment about as described in Fig. 2, fibre composition 10a is woven or is sewed up the thickness of penetrating component 14.
This configuration can make more thermosetting resin be distributed in fortifying fibre composition 14 to promote the even dipping of thermosetting fibre during curing and after solidifying.In addition, more than one fibre composition 10 is woven or penetrated to making when needed in fortifying fibre 14 other additives in different thermosetting resins and each thermoset resin fibre components 10a, b be incorporated in material 26.
The many combinations that should be understood that thermoset resin fibre components can mix to produce the goods that have the composite of desirable characteristics and be made up of it with fortifying fibre composition 14 (and contrary situation).
Fig. 4 a shows according to the composite 28 of another embodiment of the present invention, and wherein thermosetting fibre composition 10b penetrates wherein along the length of fortifying fibre layer 14.In formula, thermosetting fibre composition 10b can be identical or they some or all can be different.
Should be understood that and can use suitable technology arbitrarily to comprise that threading, braiding, stitching etc. mix thermoset resin fibre components and fortifying fibre composition.
Structure is below also included within scope of the present invention: resin fibre 10 is positioned at one or more surfaces of fibrage 14, is woven in surface placed on it or simplely.But this structure can not obtain above-mentioned all advantages substantially, those structures that especially thickness of perforating fiber layer 14 mixes, therefore do not illustrate.
Fig. 4 b has shown the composite 29 that comprises unidirectional fortifying fibre composition 31, substantially longitudinally extends by this composition 31 unidirectional heat thermosetting resin composition 10d.Fig. 4 c is the cross section of material 29, shows that thermoset resin fibre components 10d is evenly distributed in whole material 29 substantially.Fig. 4 d has shown a kind of alternative configuration, and wherein material 29 is essentially the form of layer, and thermosetting fibre 10d and the fortifying fibre of composition 31 are evenly distributed in wherein substantially.
Fig. 5 a is the schematic diagram of composite 34, and this composite 34 comprises curable thermoset resin fibre components 30, and non-fortifying fibre composition 32 is wrapped in around it with the structure of spiral substantially, and this composition 32 comprises thermoplastic in one embodiment.The known toughness that can improve thermosetting resin of thermoplastic polymer, and provide the composite 34 that comprises thermosetting and thermoplasticity blended fiber that stable material can be provided, this material then can be used to produce toughness reinforcing fibre reinforced composites goods or produce non-fibre reinforced composites and goods, such as adhesive.
There is the material 34 of fiber substantially or linear structure, also can be by braiding, threading, stitching or alternate manner and fibre reinforced materials, particularly fibrous material layer, to mix to similar mode described in embodiment above.
Thermoplastic fibre composition of the present invention can comprise one or more thermoplastic fibre.
The desirable characteristics of the composite product that the ratio of thermoset resin fibre components and thermoplastic fibre composition can be manufactured by them according to composite with finally changes and determines.
For great majority application, the ratio of thermoset resin fibres and thermoplastic fibre will be 90/10-70/30, and most preferably from about 80/20, v/v.
As shown in Fig. 5 b, thermoplasticity composition 32 can be sprinkled upon in thermoset resin fibre components 30.
Structure is below also included within scope of the present invention: substantially as shown in Figure 6, thermosetting fibre composition is wound around thermoplasticity composition, and together with thermosetting composition is interweaved with thermoplasticity composition.
Although not diagram, structure is below also included within scope of the present invention: thermosetting or the fiber-reinforced wrapped composition of thermoplastic fibre composition, its schematic diagram is similar to Fig. 5 a and Fig. 6, and figure notation 30 represents fortifying fibre composition, and 32 represent thermoplasticity or thermosetting resin composition.
The fiber-reinforced wrapped line of thermoset resin fibres or yarn can be applied to crush cutting fortifying fibre especially, and this fiber consists essentially of carbon fiber, are expressly stretched to along its length the point breaking.Special drapability and uniformity advantage are provided like this, but have not weakened in essence the structure of carbon fibre material.Have been found that the surrounding that thermoset resin fibres of the present invention is wrapped in to crush cutting fortifying fibre can stablize and strengthen crush cutting yarn.
In optional embodiment, non-fortifying fibre composition 32 comprises curing agent.
In the time that material stands condition of cure, curing agent can be enough to fully make the curing amount of thermosetting resin composition 30 to provide, and maybe can comprise a part of needed curing agent.
But preferred consolidation agent and thermosetting resin do not have or limited solidification only.This can be generally the fibre composition of solid and/or to responsive to temperature and do not show that below specified temp (material is generally held at this temperature) the limited physical contact between the curing agent of any appreciable curing characteristics reaches by two kinds.
Structure is below also included within scope of the present invention: non-enhancing ingredients 32 can be the batch mixing of (multiple) curing agent, (multiple) thermoplastic and other additives.
The present invention also provides the composite that comprises thermoset resin fibre components, non-fortifying fibre composition and fortifying fibre composition.
Fig. 7 is the composite 36 that comprises central fiber composition 38, and thermosetting fibre composition 40 and another kind of non-fortifying fibre composition 42 are wrapped in composition 38 around to form double helical form configuration at intervals with it.This structure provides stable composite, and then this material can be used for forming composite product and assembly.Material 36 make thermosetting resin composition and non-fortifying fibre composition around and distribute uniformly substantially along the length of fortifying fibre composition 38.
In optional structure, central element 38 can be thermosetting fibre composition or non-fortifying fibre composition, and another composition in them and fortifying fibre composition are so that double-helical structure is wound on it substantially.Non-fortifying fibre composition can be described above, maybe can comprise the second thermosetting fibre composition, and other thermosetting fibre compositions that this second thermosetting fibre composition can comprise with material 36 are identical or different.
Double helix structure can be taked the structure that more closely and more stretches or other suitable structures arbitrarily for equally spaced structure or its fibre composition substantially, and in these structures, each composition is preferably relative to one another around another twisting or be intertwined.
Figure 13 is the schematic diagram producing as the apparatus and method of the composite as described in about Fig. 7.
Liquid resin is dosed to two chamber V1, V2 that separate in two container V1, V2 that separate or single container.For example, V1 can add thermosetting resin formula, and container V2 can add another kind of thermosetting resin (can be identical or different composition) maybe may add thermoplastic, curing agent or these combination.Container V1 and V2 can be heated.Conventionally exert pressure with the direction of arrow P.In the base portion of container V1 and V2 or towards this base portion, be provided with hole, hole can be hole or slit (not shown), and fluent material is forced through this hole.The fiber of fortifying fibre Y or the yarn central authorities between container V1 and V2 extend, and extend to winding wheel or bobbin B from the source (not shown) of this material.Container V1 and V2, around fortifying fibre Y rotation, form the resin thread of the winding yarn Y sending from each container V1 and V2.The relative rotational of container V1 and V2 coordinates to make the structure of the resin thread on central yarn to meet the requirements with the speed of batching fiber Y on bobbin B mutually.
Fig. 8 illustrates another embodiment of the composite 43 that comprises thermosetting, thermoplasticity and fortifying fibre composition.Composite 43 comprises fibrous material layer 114 as above substantially.The line that thermosetting composition 44 is made is along the length braiding of fibrage 114 or sew up impenetrating thickness T (with the direction of arrow L), and thermoplastic fibre composition 46 penetrates in this layer, should be understood that thermosetting fibre 44 and thermoplastic fibre 46 are interchangeable.
Fig. 9 has shown another composite 48, and wherein thermosetting fibre 50 and thermoplastic fibre 52 both weave or penetrate or sew up the thickness of perforating fiber layer 114, is desirably with evenly spaced structure substantially.
In all these structures, venting quality is all fine, and be presented at setting up period, thermosetting and thermoplastic fibre are in the interior even mixing of fibrage 114 and be distributed in whole fibrage 114, thus essentially no hole, homogeneous be provided and even toughness reinforcing cured composite material goods.
Figure 10 is the cross sectional representation of composite 54, this material 54 comprises fortifying fibre composition 214, thermosetting resin composition 210 runs through into wherein, and in a side of material 54, be the layer 56 that other materials is made, this layer can comprise on the surface that is attached to fortifying fibre composition 214 or be partially immersed in resin bed wherein.
Figure 11 is the optional embodiment of display material 58, and this material comprises fortifying fibre composition 314, and thermoset resin fibre components 310 is combined in composition 314 with castellation build joint substantially.In a side of material 58, be provided with another layer of fibre reinforced materials 60, it can comprise that dry fiber maybe can comprise the partially or completely fiber reinforcement prepreg of dipping.
Figure 12 has shown another embodiment that comprises composite 62, and this material 62 has fortifying fibre composition 414, and many thermoset resin fibre components 410 are substantially to run through in composition 414 with the similar mode of embodiment of Fig. 4 a.
On a surface of fortifying fibre composition 414, there is the resin 64 of many or other more consistent models.These resins can supplement thermoset resin fibre components 410, thereby guarantee suitable dipping in whole fortifying fibre composition 414 of thermosetting resin during curing and soak.Drop of resin or model 64 (to be similar to layer 56 the mode of embodiment of Figure 10) also provide the surface bonding with relative dry composite substantially, thereby contribute to place, composite is cured or the during curing placement of composite.
All composites discussed above can be manufactured to not containing any curing agent or there is no enough curing agent, in the case, need to promote the curing curing agent of thermoset resin fibre components away from material until in the time solidifying generation.As mentioned above, curing agent generally comprises catalyst and curing agent, and by being similar to the technology of resin perfusion and well known to a person skilled in the art other technologies after " laying (lay up) " or be directed into mould during lay-up process in or on the composite of the lip-deep light liquid form of utensil.
Because the viscosity of curing agent is very low, they also can be by such as spraying, or other technologies that apply etc. apply, but particularly can not apply vacuum condition about the latter, its preferably lamination alternately between composite, implement solidify.
Following structure is also included within scope of the present invention: as mentioned above, some or all of curing agent are set to a part for composite.For these embodiments, curing agent can be solid or have in addition high viscosity to avoid or to stop its movement in material under preservation condition, and/or they can be thermally sensitive or be present in composite with the state of relative inactivation in addition.
In one embodiment, curing agent can be the form of fibre composition or particle, and is present in above-mentioned composite, but becomes to separate to avoid unwanted early stage interaction and solidify with thermosetting fibre.For example, if the form that curing agent is fiber, it one of can comprise in the fibre composition 40,42 of the embodiment in Fig. 7, and another composition is and its thermosetting resin composition separately.The non-storage of application, solidify or precuring condition after, curing thereby thermosetting and curing agent fibre composition will melts and merge generation.The effect of fortifying fibre composition is that the thermoset resin fibre components in material and curing agent are separated.
Figure 14 is suitable for forming according to the schematic diagram of another device of composite of the present invention.This device is very similar to known device in the conventional prepreg of formation.The fiber that improvement is to be fed in composite comprises the thermoset resin fibres of not mentioning in the past.
In Figure 14, show three kinds of sources 1,2,3 of fiber, be provided for from each source forming according to the fibrous material of composite of the present invention.
For example, 1 source that can comprise according to thermoset resin fibre components of the present invention, source.Source 2 and 3 also can comprise fortifying fibre composition, other non-fortifying fibre compositions, other thermoset resin fibre components or other various combinations.
Thereby substantially feed in raw material and be packaged together to form composite around rotary drum D1, D2 and by roller R1, R2 from the fibre composition in each source 1,2,3, then composite is according to routine techniques, and such as other resin beds of application, supporting substrate etc. further processed.
The device of Figure 14 is suitable for, for example, form about Fig. 4 a, 4b, 4c, 4d the composite described in Figure 12.In addition, can comprise and sew up to produce the composite as shown in for example Fig. 3 and Fig. 8 by installing the further processing of composite of 14 generations.
Material of the present invention also can be used for piddler Shu Fangfa.Figure 16 is that thermosetting fibre composition of the present invention is for the intrafascicular application schematic diagram of piddler.
This device is generally the conventional equipment for piddler bundle.But thermosetting fibre is dosed to placement head H along fortifying fibre and curing agent fiber (or more thermosetting fibre or arbitrarily other fibers).Then mandrel M is located and be wound to three kinds of fibre compositions that are dosed to placement head H above, and M rotates to be wound around around its axle.Placement head H moves up and down to guarantee the uniform winding of fiber along the length of mandrel M.
The number and the character that should be understood that the fiber that is dosed to placement head can change according to character and the number of the fiber that will be wound around on mandrel M.For example, an above thermosetting fibre composition can be dosed to placement head H.These many thermosetting fibre compositions can be identical or different mutually.The number of fortifying fibre and character can change.Curing agent can not provide with fibers form, and can otherwise apply, and for example, as mentioned above, curing agent can be arranged in fortifying fibre composition and/or thermosetting fibre composition.In addition can use non-fortifying fibre composition.
According to the present invention, for using piddler bundle technology can adopt a large amount of selection modes and modification, and apparent for those skilled in the art with the advantage of this utilization thermoset resin fibre components.
Under the prerequisite that does not deviate from the spirit or scope of the present invention, can make many changes.
It being understood that in the embodiment of mentioning in the above, the number of illustrated thermosetting and non-fortifying fibre composition is especially little.Although the composition that comprises single fiber and the single fibre composition that use comprise within the scope of the invention, the present invention conventionally relate to more composite of the present invention comprise many, individual even several thousand fibre compositions of possible hundreds of.
To further understand that can use thermoset resin fibre components of the present invention to produce the composite of many kind structures, above-mentioned embodiment is only to select for remarkable advantage, the application of wide region and a kind of selection mode of structure of the material that can produce according to the present invention are described.
For many application of the present invention, the general preferred following composite that provides: all thermosetting fibre compositions are evenly distributed in whole or substantially in whole composite, thereby for the manufacture of the composite product that shows that in total character is consistent.
But, for specific application, the distribution of different fibre compositions can be inhomogeneous wittingly, and can select the forming component material of uneven distribution therein, can produce thus its some scopes or region and have the goods of the custom-designed characteristic that is different from other scopes or region.Composition of the present invention and the especially fiber properties of thermosetting resin composition contribute to produce this type of material and goods.
For example, illustrated in the above and illustrated thermosetting and/or non-enhancing ingredients with reference to accompanying drawing, owing to extending by thickness T and along length L, they can be set to only some sections along a part of length, length extends, only midway by this thickness etc.Certainly, this type of material also has certain width conventionally, often takes substantially layer or the form of plate, and composition can only be arranged on preposition or along the region on this width.
The fibers form of composition makes composition be easy to provide with this selection mode.For example, they can be sewed up in fortifying fibre at preposition place, and/or weave or penetrate in addition to the matrix of fortifying fibre.In addition specifically can be arranged on along be scheduled to and region interval in the length of central element with reference to Fig. 5 and the illustrated composition of Fig. 7.
Also can be as adhesive and other non-fibre reinforced materials according to composite of the present invention.Foregoing embodiment herein, specifically those embodiments that lack any fortifying fibre composition can be used for this application.
Although give prominence to hardy those features of the present invention that are considered to particular importance in the description above; but should note the applicant claimed feature of any patentability or the combination of these features above-mentioned and/or that show in the accompanying drawings, no matter whether emphasize.
Claims (13)
1. one kind has the composite of linear structure, comprise curable thermoset resin fibre components and fortifying fibre composition, described curable thermoset resin fibre components and described fortifying fibre composition mix, wherein one or more curable thermoset resin fibres around and twist together along the length of one or more fortifying fibre composition.
2. composite according to claim 1, wherein said curable thermoset resin fibre components comprises many curable thermoset resin fibres.
3. composite according to claim 1, wherein the ratio of curable thermoset resin fibre components and fortifying fibre composition is 50:50-10:90v/v.
4. composite according to claim 2, wherein the ratio of curable thermoset resin fibre components and fortifying fibre composition is 50:50-10:90v/v.
5. a composite, comprise curable thermoset resin fibre components and fortifying fibre composition, wherein curable thermoset resin fibres layer and fortifying fibre layer are contacting with each other at least one surface separately, and wherein one or more curable thermoset resin fibres around and twist together along the length of one or more fortifying fibre composition.
6. according to the composite described in any one in claim 1-5, wherein said curable thermoset resin fibre components comprises one or more thermoplastics that can make described curable thermosetting fibre composition toughen in the time solidifying.
7. according to the composite described in any one in claim 1-5, wherein said curable thermoset resin fibre components comprises curing agent.
8. according to the composite described in any one in claim 1-5, wherein said curable thermoset resin fibre components comprises and is kept at refrigeration or freezing conditions repressed curing agent of lower time when described curable thermoset resin fibre components.
9. according to the composite described in any one in claim 1-5, the viscosity of wherein said curable thermoset resin fibre components at 23 ℃ of temperature is greater than 5 × 10
4pas.
10. according to the composite described in any one in claim 1-5, wherein said curable thermoset resin fibre components comprises N, N, N, N-four glycidyl group-4'4-diaminodiphenyl-methane and polyether sulfone.
Manufacture the method for composite product for 11. 1 kinds, comprise and make the composite described in any one in claim 1-10 stand condition of cure.
12. methods according to claim 11, wherein said curable thermoset resin fibre components or composite mix in the time starting curing process with curing agent.
13. according to the method described in claim 11 or 12, and wherein curing agent is included in described composite, and promotes its solidification by applying condition of cure.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210459246.6A CN102977387B (en) | 2007-07-20 | 2008-07-10 | Thermoset resin fibres |
Applications Claiming Priority (3)
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| GB0714224A GB2451136B (en) | 2007-07-20 | 2007-07-20 | Thermoset resin fibres |
| GB0714224.3 | 2007-07-20 | ||
| PCT/GB2008/002378 WO2009013458A2 (en) | 2007-07-20 | 2008-07-10 | Thermoset resin fibres |
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| CN201210459246.6A Division CN102977387B (en) | 2007-07-20 | 2008-07-10 | Thermoset resin fibres |
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| CN101784703B true CN101784703B (en) | 2014-06-11 |
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| EP3199674B1 (en) | 2018-09-19 |
| US8883305B2 (en) | 2014-11-11 |
| CA2693240A1 (en) | 2009-01-29 |
| US8084126B2 (en) | 2011-12-27 |
| CN102977387A (en) | 2013-03-20 |
| CA2693240C (en) | 2015-05-26 |
| CN101784703A (en) | 2010-07-21 |
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